Ammonium Chloride → HCID 66731141, compound

Participants

Reaction Steps

Methyllithium (63 ml of a 1.6M solution in diethyl ether, 0.10 mol) was added over 1 h to a solution of crude 5-hydroxy-2,2,7,7-tetramethyltricyclo[6.2.1.01.6]undecan-4-one (4, 20 g, obtained as in Example 1c) in diethyl ether (200 ml), cooled below 10° C. After 1.5 h stirring, an additional portion of methyllithium (50 ml of a 1.6M solution in diethyl ether, 0.080 mol) was added and stirring continued overnight at room temperature. The reaction mixture was poured onto a stirred mixture of saturated aqueous solution of ammonium chloride (200 ml) and ice (100 g), the phases separated and the aqueous phase extracted with MTBE (200 ml). The combined organic phases were washed with water (3×200 ml), dried (Na2SO4), concentrated in vacuo and the residue (21 g) purified by flash chromatography (MTBE/hexane 1:3 to 1:2) to afford 2,2,4,7,7-pentamethyltricyclo[6.2.1.01.6]undecane-4,5-diol (5b, 5.7 g, ˜46% yield starting from 3, white solid).

Provenance & Evidence